What obstacles did john
f. kennedy need to over come?

The Bay of Pigs Invasion 1961
Communism
President Kennedy faced a confident Soviet Union, and the Peoples Republic of China. Fears of Communists expansion frightened America.
The Cuban Missile Crisis
The National Security archive at George Washington University, went to a lot of trouble to focus understanding of the Cuban Missile Crisis, Which was the Bay of Pigs.
The PT-109 Incident 
August 2, 1943 John F Kennedy was in his PT boat until Japanese PT boats attacked the PT-109. The ship sank killing 2 members but carried out the others alive.